• 1. An investigation of surface properties, local elastic modulus and interaction with simulated pulmonary surfactant of surface modified inhalable voriconazole dry powders using atomic force microscopy
  Michael Kappl,Paul M. Young,Daniela Traini,Sanyog Jain RSC Adv., 2016,6, 25789-25798
• 2. An investigation on the second-order nonlinear optical response of cationic bipyridine or phenanthroline iridium(iii) complexes bearing cyclometallated 2-phenylpyridines with a triphenylamine substituent?
  David B. Cordes,Alexandra M. Z. Slawin,Stefania Righetto,Denis Jacquemin,Eli Zysman-Colman,Véronique Guerchais Dalton Trans., 2018,47, 8292-8300
• 3. An investigation on the interaction modes of a single-strand DNA aptamer and RBP4 protein: a molecular dynamic simulations approach?
  Raheleh Torabi,Hedayatollah Ghourchian,Massoud Amanlou Org. Biomol. Chem., 2016,14, 8141-8153
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  Lab Chip, 2019,19, 524-535
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  Kathrin Kutlescha,Rhett Kempe New J. Chem., 2010,34, 1954-1960

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acid esters
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Benzoic acid esters
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Methyl 5-fluoro-2-hydroxybenzoate (CAS No. 391-92-4): A Comprehensive Overview

Methyl 5-fluoro-2-hydroxybenzoate, identified by its CAS number 391-92-4, is a compound of significant interest in the field of pharmaceutical chemistry and biochemistry. This ester derivative of fluoro-substituted hydroxybenzoic acid has garnered attention due to its unique structural properties and potential applications in drug development. The presence of both a fluoro group and a hydroxyl group in its molecular structure imparts distinct chemical reactivity, making it a valuable intermediate in synthetic chemistry.

The compound’s molecular formula, C₈H₇FO₃, reflects its composition and suggests a range of possible functional interactions. The fluoro group, known for its ability to modulate metabolic pathways and enhance binding affinity, plays a crucial role in the pharmacological activity of many therapeutic agents. In contrast, the hydroxyl group contributes to hydrogen bonding capabilities, which are essential for interactions with biological targets such as enzymes and receptors.

Recent studies have highlighted the utility of Methyl 5-fluoro-2-hydroxybenzoate in the synthesis of novel pharmaceuticals. Researchers have explored its role as a precursor in the development of fluoroquinolone analogs, where the fluoro substituent enhances antibacterial efficacy. Additionally, its incorporation into heterocyclic compounds has shown promise in the design of kinase inhibitors, which are critical for treating cancers and inflammatory diseases. The compound’s ability to serve as a building block for more complex molecules underscores its importance in medicinal chemistry.

The chemical synthesis of Methyl 5-fluoro-2-hydroxybenzoate involves multi-step processes that often require precise control over reaction conditions. One common synthetic route involves the esterification of 5-fluorosalicylic acid with methanol under acidic catalysis. This method leverages the reactivity of carboxylic acids to form esters, a fundamental transformation in organic synthesis. Advances in catalytic systems have improved the efficiency and selectivity of these reactions, enabling higher yields and purer products.

In addition to its synthetic significance, Methyl 5-fluoro-2-hydroxybenzoate has been investigated for its potential biological activities. Preliminary studies suggest that derivatives of this compound may exhibit antioxidant properties, which could be beneficial in preventing oxidative stress-related diseases such as neurodegenerative disorders. Furthermore, the fluorine atom’s electronic effects may influence ligand-receptor interactions, making it a candidate for designing drugs with improved pharmacokinetic profiles.

The role of computational chemistry in understanding the behavior of Methyl 5-fluoro-2-hydroxybenzoate cannot be overstated. Molecular modeling techniques have allowed researchers to predict how this compound interacts with biological targets at an atomic level. These insights are invaluable for rational drug design, enabling scientists to optimize molecular structures for enhanced binding affinity and reduced side effects. The integration of experimental data with computational methods has accelerated the discovery process in pharmaceutical research.

The industrial production of Methyl 5-fluoro-2-hydroxybenzoate requires stringent quality control measures to ensure consistency and purity. Analytical techniques such as high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy are routinely employed to verify product quality. These methods provide detailed information about the compound’s chemical structure and purity, ensuring that it meets the standards required for pharmaceutical applications.

The future prospects for Methyl 5-fluoro-2-hydroxybenzoate are promising, with ongoing research exploring new derivatives and applications. The growing demand for fluorinated compounds in drug development continues to drive innovation in synthetic methodologies. As our understanding of molecular interactions deepens, compounds like this are likely to play an increasingly important role in addressing unmet medical needs.

• 331729-57-8(Benzoic acid, 5-fluoro-2-(phenylmethoxy)-, phenylmethyl ester)
• 851664-22-7(Benzoic acid, 2-[(4-fluorophenyl)methoxy]-, methyl ester)
• 1737-21-9(Ethyl 4-fluoro-2-hydroxybenzoate)
• 443-12-9(Ethyl 5-Fluoro-2-hydroxybenzoate)
• 70163-98-3(Methyl 3-fluoro-2-hydroxybenzoate)
• 392-04-1(Methyl 4-fluoro-2-hydroxybenzoate)
• 753922-57-5(Benzoic acid, 4-fluoro-2-(phenylmethoxy)-, methyl ester)
• 151793-20-3(Methyl 5-fluoro-2-methoxybenzoate)
• 204707-42-6(Methyl 4-fluoro-2-methoxybenzoate)
• 180068-67-1(Methyl 3,5-difluoro-2-hydroxybenzoate)